Carbon Dioxide → HCID 13882105, compound

HRID 543039Notes

Reaction equation

HRID 543039 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].C1(=O)O[CH2:15][CH2:14][O:13]1.C(=O)=O>N1C=CN=C1.C(OCC)C>[OH:13][CH2:14][CH2:15][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:9])=[O:10]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 7303Ethylene carbonateHCID 6375462-Hydroxybenzene-1-sulfonamide2×

Product 1

HCID 13882105HCID 13882105, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 795ImidazoleCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 74.6 g (0.43 mol) of 2-hydroxybenzenesulfonamide, 45.3 g (0.51 mole) of ethylene carbonate and 0.9 g of imidazole was heated to 160° with vigorous stirring. After about four hours the carbon dioxide evolution had subsided and no unreacted 2-hydroxybenzenesulfonamide was present in the reaction mixture. The mixture was allowed to cool and about 400 ml of diethyl ether was added to the thick oil. The two-phase mixture was stirred vigorously and was heated to reflux for about one hour. The diethyl ether was decanted off and a fresh portion of diethyl ether was added. The mixture was again stirred and heated to reflux. After the diethyl ether was decanted off a fresh portion of diethyl ether was added and the mixture was allowed to stand at ambient temperature for about 18 hours. The resulting light brown solid was isolated by filtration and was recrystallized from nitromethane to afford 49 g (53%) of the title compound; m.p. 94°-99° C. The infrared spectrum exhibited a broad peak at approximately 3400 cm-1 consistent with the primary alcohol of the product and peaks at 3370 cm-1 and 3270 cm-1 consistent with the NH2 of a primary sulfonamide.

Workup

  1. temperaturewas heated to 160° with vigorous stirring
  2. temperatureto cool
  3. temperaturewas heated
  4. temperatureto reflux for about one hour
  5. customThe diethyl ether was decanted off
  6. additiona fresh portion of diethyl ether was added
  7. stirringThe mixture was again stirred
  8. temperatureheated to reflux
  9. customAfter the diethyl ether was decanted off a fresh portion of diethyl ether
  10. additionwas added
  11. customThe resulting light brown solid was isolated by filtration
  12. customwas recrystallized from nitromethane

Sources & evidence

ORD record
ord-80d7811aa63c4e8db7120ffe3c8199fe
Source dataset
uspto-grants-1987_04
Patent number
US04661146

Reaction notes

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